Why Amazon, Google, and OpenAI Are Fighting Over Your Next Purchase

The agentic shopping wars are here. And nobody's paying attention yet.

Amazon just sued Perplexity. Google just launched agentic shopping. OpenAI is rewriting how commerce works...all of it is aimed at the holiday season, and all of it means something fundamental about e-commerce is about to shift.

But here's what's getting lost in the headlines: this isn't just about the tech. It's a legal story about who owns your customer relationship, amd a business model story about who controls the data. It's a fork in the road for SMBs between two very different futures - one where they're dependent on platforms, and one where they might finally level the playing field.

The narrative says conversational commerce is the future of shopping. But what the platforms are really fighting about is whether you'll shop within their walls or whether you'll shop with an agent that can see everywhere. The winners won't be decided by technology. They'll be decided by who wins the lawsuit and who controls the infrastructure.

In this episode:

• What conversational commerce actually is (and why "shopping at the point of inspiration" changes everything)
• The Amazon vs. Perplexity lawsuit
• Why Amazon's walled garden strategy is essentially them behaving like a legacy media company
• Google's brilliant hedge: how they're playing both open and closed systems simultaneously
• Attribution, data ownership, and why SMBs have been losing money to platforms for 20 years
• Why merit-based product discovery could finally be possible again
• The legal and regulatory implications of this battle (feat. Nathalie's lawyer brain)
• What SMBs actually need to do to stay relevant across both walled gardens and open systems
• Plus: Yann LeCun leaving Meta, OpenAI finally fixing the em dash problem, and why AI performance reviews are creating a trust crisis

Timestamps:

00:00 What We've Been Up to This Week

07:53 Welcoming Nathalie to the podcast

09:36 Shopping at the Point of Inspiration: What Conversational Commerce Actually Means

13:52 When AI Becomes Your Personal Shopping Assistant

14:11 Why Now? The Timing of Conversational Commerce

15:34 The Death of Shopping Friction

18:00 Follow the Money: Who Profits When AI Owns the Customer Relationship

19:31 Amazon vs. Perplexity: The Lawsuit That Could Reshape Retail

24:56 Walled Gardens vs. Open Rails: The Fork in the Road for Commerce

31:27 How Products Get Discovered Without Paid Ads

37:23 Google's Hybrid Approach to Shopping

40:53 Understanding the Two-Tier Internet

45:04 Navigating the New Landscape for SMEs

48:26 AI News: Yann LeCun's Departure from Meta

51:47 AI News: OpenAI Finally Fixes the Em Dash

55:52 AI Gone Wrong: When JPMorgan Let AI Judge Your Performance

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